Catching up with comedian Vinnie Penn

Nutmeggers who have turned their radios on over the past 20 years are probably familiar with Vinnie Penn.

He’s a DJ with a weekday morning talk show called “The Vinnie Penn Project” on iHeartradio affiliate station 960/WELI and a 25-year veteran comedian — though, according to Penn, a few of his former teachers may argue he got his start at a desk in grade school.

“CT radio listeners, both when I was doing Top 40 and now doing news/talk, are the best,” Penn said via email.

“Especially when they give me a hard time like we’ve known each other for 20 years, which many will say is exactly what it feels like.”

His next gig, however, is off the airwaves as a headliner for Next Stop: New Haven, a virtual fundraiser to benefit the Shubert Theater. The theme is “Late Nite,” giving adults the chance to enjoy a “night out” while staying in.

The program will feature a stand-up show from Penn, musical entertainment from “Broadway’s rising stars” and cocktail demonstrations from Ordinary.

Penn chatted with Hearst Connecticut Media via email about pandemic comedy and what to expect from “Next Stop: New Haven.”

Sarajane Sullivan: The pandemic has changed a lot of things, especially in the entertainment industry. How has it affected you as a comedian? Are there benefits you prefer about performing virtually?

Vinnie Penn: There are virtual events that I’ve thought were fantastic (like I expect this one to be) and some virtual efforts that I thought came up woefully short. I’ve seen some great concerts but some insanely awkward daytime TV.

The pandemic has obviously affected my ability to do a live show, but I wouldn’t sell pre-taped comedy short. The comedian is SO much more at ease — even the ones who thrive

on immediate, positive feedback (which is all of us really) — that once you get over there being no “live studio audience” you just get in the zone and deliver.

SS: Who are your three comedy heroes?

VP: I love this question! Sam Kinison is tops for sure. Seinfeld, definitely. Then probably Chris Rock.

SS: Can you give us a sneak peek at some of the topics you’ll cover during the event?

VP: I want to keep the focus on our stages and Broadway, and reflect on this time without them, but I’ve a gut feeling quarantine with my kids and my recent divorce may sneak in!

Plus some highlights from all the times I’ve attended shows at the theater.

SS: Why are you participating in this fundraiser? Why is it important to you?

VP: I love The Shubert. I have so many fantastic memories of The Shubert, from me first going there as a kid to me taking my own kids there.

I’ve met some TV heroes there (Judd Hirsch, Valerie Harper, to name a few) and have always felt its connection to New York. I’ve also always felt it is quite the viable alternative to New York.

SS: Things have been heavy this last year, to say the least. Do you feel comedy has helped alleviate some of that weight for your audience? If so, has that been a burden for you as a comedian or is it something you take on naturally?

VP: I can find laughs in anything but I’d be lying if I said this past year, even if I was doing that, a whole lot of people weren’t and weren’t interested in doing it either.

I’ve watched TV at home with my kids and we’ve roared with laughter. I think it’s helped them during this bizarre time. They’re teenagers and going to school in their bedrooms. There are a lot of days they NEED laughs, and they’re sick of my routine.

We re-watched all of “New Girl” and it killed. We just loved it. We had a stretch of “Golden Girls” in there, too. I take it on naturally but do it well aware that some people might not be in the mood to laugh. I hope those who stream this event want to.

SS: What are you most excited for concerning your role in this event?

VP: The inevitable rave reviews.

SS: If you had to convince someone who’s on the fence to attend this event, what would you tell them? VP: You can start “The Queen’s Gambit” or “Bridgerton” the next day. They’ll be there. What took you so long, anyway?

Next Stop: New Haven takes place at 8:30 p.m. Thursday, Feb. 11, online. Tickets cost $75 and include a link to the virtual show, a curated box of beverages with ingredients for the cocktail demonstrations and small bites from local restaurants, all portioned for two people. The theater will contact attendees to coordinate curbside box pickup the afternoon of the show. For tickets and information, visit shubert.com.

Contributed photo Vinnie Penn